Acetophenone → 1-Phenylethanol, (S)-

HRID 1525138Notes

Reaction equation

HRID 1525138 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CC([O-])(C)C.[K+]>[Ru].CC(O)C>[C:4]1([C@@H:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 7410AcetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 4431351-Phenylethanol, (S)-

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
30 °C

Procedure

Under nitrogen stream, acetophenone (20 mmol), RuCl[(S)-xylbinap][(S)-daipen] (1/100 molar fold of acetophenone) and t-BuOK (5 molar folds of the ruthenium catalyst) were added to a Schlenk tube. 2-propanol (8.3 mL per 100 mg of acetophenone) was added, then stirred for 10 minutes at 30° C. As a result of analysis of the reaction mixture by gas chromatography (Chirasil-DEX CB), it was found that the conversion rate is 94%, and the optical purity is 98.4% ee.

Workup

  1. customAs a result of analysis of the reaction mixture by gas chromatography (Chirasil-DEX CB), it

Sources & evidence

ORD record
ord-1e9c3a54f4b54e6189ca860d34bd05d2
Source dataset
uspto-grants-2015_07
Patent number
US09079931B2

Reaction notes

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